1,4-Naphthoquinone → 2,3-Dihydro-1,4-naphthoquinone
Reaction equation
[CH:1]1[CH:2]=[CH:3][C:4]2[C:11](=[O:12])[CH:10]=[CH:9][C:7](=[O:8])[C:5]=2[CH:6]=1>C(Cl)Cl>[C:7]1(=[O:8])[C:5]2[C:4](=[CH:3][CH:2]=[CH:1][CH:6]=2)[C:11](=[O:12])[CH2:10][CH2:9]1Participants
3
Reactant 1
Product 1
Reagents, catalysts & solvents 1
Procedure
According to the general procedure, a solution of naphthoquinone (50 mg, 0.31 mmol) and rac-32 (10.0 mg, 0.0063 mmol, 2.0 mol %) in CH2Cl2 (3 mL) was pressurized with H2 to 62 bar and stirred for 72 h. Filtration of the reaction mixture and evaporation of the solvent gave the crude product, which was purified by column chromatography (30% EtOAc in hexane, silica gel) to give 47 (45 mg, 89%) as a 2:1 mixture of 2,3-dihydronaphthalene-1,4-dione and 1,4-dihydronaphthalene-1,4-diol. 1H NMR (300 MHz, acetone-d6, 2,3-dihydronaphthalene-1,4-dione33): δ 8.00-7.97 (m, 2H), 7.83-7.81 (m, 2H), 3.11 (s, 4H); 1,4-(dihydronaphthalene-1,4-diol34): δ 8.32 (bs, 2H), 8.18-8.15 (m, 2H), 7.47-7.43 (m, 2H), 6.73 (s, 2H).